The Kristen Boss Podcast

Episode 229: "I'm Back!"

Host: Kristen Boss
Date: September 8, 2025

Episode Overview

In this long-awaited return, Kristen Boss candidly shares her journey during a nearly year-long hiatus from the podcast. After stepping back to heal and gain clarity, Kristen reflects on what led her to pause, her insights into the pitfalls of personal branding, and her evolution as both a person and entrepreneur. She discusses rebuilding with intention, the courage required for true pivots, and the lessons learned from both triumphs and pain. This episode sets the stage for a new, honest chapter—inviting listeners to join her as she unpacks "the implosion," her healing, and what it means to chase meaningful, sustainable success beyond the metrics.

Key Discussion Points & Insights

1. Why Kristen Stepped Away

• Kristen describes her decision as a needed "healing journey," believing she was closing the podcast chapter for good after feeling depleted, misaligned, and creatively empty.
• “I thought, you know, it was a good run, it was great. And I think at the time I thought, oh, there’s, there’s nothing left for me to say.” (02:07)
• She humorously shares spending time on hobbies like "paint by number" and imagining a rural life, reflecting on how unexpected healing can bring new perspectives and surprising returns.

2. Clarity, Rest, and the Creative Itch

• Time away gave her perspective, but she found “the itch to build and create” resurfaced sooner than anticipated.
• Kristen admits feeling out of practice recording solo and requests "grace" from listeners as she re-acclimates to podcasting.

3. The Trap of Building a Personal Brand

• Kristen speaks vulnerably about her previous business:
  • She unintentionally “commoditized” herself, becoming the literal product people bought.
  • “What I had inadvertently done was also dehumanized myself in the sense of like, I am the thing that people buy. Therefore, I have to make myself as palatable as possible so that people will continue to buy from me.” (15:05)
• She discusses the pressures and burnout that come from this model, highlighting how burnout isn’t always a result of hours worked, but often of misalignment:
  • “I was so exhausted…my burnout was actually an alignment issue.” (18:37)

4. The Ugly Side of Pivoting

• Kristen is honest about the difficulty of her pivot:
  • “There was nothing noble or beautiful about the pivot. It was like, knockthem out, drag them out, cry, lots of therapy…it had to be pried from my white knuckled grip.” (22:26)
• She notes many people, after painful experiences, make unconscious “agreements” to avoid repeating those pains—even if these new arrangements are also limiting.

5. Swinging to the Other Extreme

• Initially, Kristen swung from centering her brand around herself to wanting to become “so anti personal brand,” building a “faceless” company.
• This, too, felt hollow: “It lacked soul, it lacked the story, it lacked the why. And part of that is because I was holding my why close.” (29:24)
• She confesses to figuratively and literally hiding, not sharing her true why or full story.

6. Being Ready to Tell the Full Story

• Kristen waited to share her story until she could do so from the “right place”—not for shock, sympathy, or monetization.
  • “I didn’t want to prostitute my story. I didn’t want to take my story and dishonor it by thinking, cool, how can I monetize this?...I was going to hold the story until it felt like the right time…” (34:10)
• Support from mentors helped her realize the importance of bringing her full story into her work.

7. Learning from Rock Bottom

• Kristen will chronicle her “implosion” and what she learned, aiming to tell the unvarnished truth.
  • “If I have to tell the cautionary tale, I will. If I’m going to tell the truth, I will.” (43:47)
• She reckons with the irony of having written a book on anti-hustle, only to find herself succumbing to hustle at a deeper level:
  • “Even though I wrote the book on anti hustle, I still broke from the hustle again…it was sneaky, it was subtle, it was cunning.” (47:02)
• She reframes her identity: “Maybe I am the poster child for what the constant work of returning to ourselves and recovering…what does it look [like] to be a recovering hustle hustler?” (49:19)

8. Preview of What’s Next

• Kristen will share her story in chapters:
  • Leading up to the implosion
  • The ignored warning signs
  • The event itself
  • Healing, pivot, and the “now”
• She emphasizes this will be a “learning season,” not a “winning season”—with messy, gritty honesty rather than aspirational shine:
  • “It’s a learning season. And it is gritty. It is hard. I’ve been crying a lot, which I think is good. Even my therapist is like, you’re feeling. I’m like, how do I unsubscribe from this part?” (58:42)

9. Lessons on Success and Fulfillment

• Kristen likens her journey to The Wizard of Oz, believing the “Emerald City” (wealth, achievement) would solve her problems, but finding a different reality:
  • “I feel like entrepreneurship was the Emerald City…If you could put a price tag on the Emerald City, I would have said, you know, making a million dollars, if once I make a million, all of my problems are going to go away. And what’s interesting is that was not the case…” (1:03:05)
  • She underscores no external achievement resolves internal misalignment: “Nothing we can do externally can solve an internal problem.” (1:10:34)
• Despite challenges, Kristen affirms her belief in entrepreneurship—“It’s about who we are becoming…it’s how we are handling adversity…not the wins alone.”

10. Invitation to Listeners

• Kristen’s message now includes:
  • “How do we protect our peace while pursuing our purpose?”
  • Gritty, real stories and warning signs for those in both “winning” and “learning” seasons.
• She asks for grace as she tells her story, aiming to save others from the “hard lessons” she endured:
  • “If I could save you the pain, I’m going to. So whatever season you’re in, you’re invited into this.” (1:14:02)

Notable Quotes & Memorable Moments

• “What I had inadvertently done was also dehumanized myself in the sense of like, I am the thing that people buy. Therefore, I have to make myself as palatable as possible so that people will continue to buy from me.” (15:05)
• “My burnout was actually an alignment issue.” (18:37)
• “There was nothing noble or beautiful about the pivot. It was like, knock them out, drag them out, cry, lots of therapy…it had to be pride from my white knuckled grip.” (22:26)
• “I didn’t want to prostitute my story. I didn’t want to take my story and dishonor it by thinking, cool, how can I monetize with this?...I was going to hold the story until it felt like the right time…” (34:10)
• “If I have to tell the cautionary tale, I will. If I’m going to tell the truth, I will.” (43:47)
• “Even though I wrote the book on anti hustle, I still broke from the hustle again…it was sneaky, it was subtle, it was cunning.” (47:02)
• “Maybe I am the poster child for…what does it look [like] to be a recovering hustle hustler?” (49:19)
• “It’s a learning season. And it is gritty. It is hard.” (58:42)
• “Nothing we can do externally can solve an internal problem.” (1:10:34)
• “If I could save you the pain, I’m going to. So whatever season you’re in, you’re invited into this.” (1:14:02)

Timestamps for Key Segments

• 00:00–06:00 — Kristen returns, reflecting on hiatus and initial uncertainty
• 06:00–11:00 — Healing journey and surprising rediscovery of the urge to create
• 11:00–21:00 — The dangers of accidentally commoditizing yourself and experiencing burnout through misalignment
• 21:00–29:00 — The struggle and resistance of the pivot; "ugly" transitions and learning to let go
• 29:00–34:30 — Swinging to the “faceless” brand; holding her "why" too closely, hiding from her audience
• 34:30–41:00 — Deciding when and how to share the full story; not “prostituting” her experience
• 41:00–52:00 — The realities of rock bottom post-success; lessons that will shape the series of coming episodes
• 52:00–01:03:00 — The Emerald City metaphor—success, disappointment, and the limitations of external achievement
• 01:03:00–end — Embracing entrepreneurship anew, what listeners can expect, and an invitation to future gritty, honest episodes

Closing Thoughts

Kristen’s return is marked by honesty, humility, and a clear intent to serve others facing their own pivots, burnout, and existential business questions. She promises a “learning season”—shedding aspirational distance for relatable truths. The stage is set for a series of raw, insightful episodes about sustainable success, leadership, pivoting through pain, and building a life (not just a business) that can withstand anything.

Listeners are invited to come along, whether they’re at the top, bottom, or somewhere in the unpredictable in-between.